Dimethylformamide → 3,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 972513Notes

Reaction equation

HRID 972513 reaction equation
[C:1]([CH:3]([C:7]1[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH:8]=1)[C:4]([NH2:6])=[O:5])#[N:2].[CH3:14]N(C)C=O.C(OCC)(OCC)OCC>C(OCC)(=O)C>[O:5]=[C:4]1[C:3]([C:1]#[N:2])=[C:7]2[C:8]([C:9](=[O:13])[CH2:10][CH2:11][CH2:12]2)=[CH:14][NH:6]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31214Ethyl orthoformateHCID 21404771alpha-Cyano-3-oxo-1-cyclohexen-1-acetamide

Product 1

HCID 222665143,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

75 parts of α-cyano-3-oxo-1-cyclohexen-1-acetamide in 400 parts by volume of dimethylformamide and 75 parts of triethyl orthoformate are heated on a steam bath for 3 hours to 16 hours. Solvent was then removed in vacuum to give a syrup which is taken up in ethyl acetate. Cooling of this solution gives 2,3,5,6,7,8-hexahydro-3,8-dioxo-4-isoquinolinecarbonitrile which is identical to the product of Example 3.

Workup

  1. customSolvent was then removed in vacuum
  2. customto give a syrup which
  3. temperatureCooling of this solution

Sources & evidence

ORD record
ord-86a4e7b6a67e453ab6b924e3b0a890be
Source dataset
uspto-grants-1977_10
Patent number
US04053476

Reaction notes

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